Hydrochloric Acid → 3-Allyl-4-hydroxybenzoic acid

HRID 2294968Notes

Reaction equation

HRID 2294968 reaction equation
C([O:3][C:4](=[O:15])[C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([CH2:12][CH:13]=[CH2:14])[CH:6]=1)C.[OH-].[Na+].Cl>O>[CH2:12]([C:7]1[CH:6]=[C:5]([CH:10]=[CH:9][C:8]=1[OH:11])[C:4]([OH:15])=[O:3])[CH:13]=[CH2:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 12252872Ethyl 3-allyl-4-hydroxybenzoate

Product 1

HCID 109650813-Allyl-4-hydroxybenzoic acidYield 91%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethyl-3-allyl-4-hydroxybenzoate (1.03 g) was added to a cold solution of sodium hydroxide pellets (0.8 g) in water (10 ml) and the mixture was stirred for 18 hours. 2N aqueous hydrochloric acid was added to acidify the reaction mixture and to give a solid which was extracted into dichloromethane. The organic phase was separated, washed with water, saturated brine and dried (MgSO4). Evaporation gave 3-allyl-4-hydroxybenzoic acid (0.81 g) as a solid, m.p. 119°-123° C.; microanalysis, found C, 66.1; H, 5.9%; C10H10O3 0.2H2O requires: C, 66.1; H, 5.77%; NMR(DMSO-d6): 3.31(2H,d), 4.95-5.17(2H,m), 5.85-6.05(1H,m), 6.85(1H,d), 7.55-7.75(2H,m), 10.15(1H,s), 12.30(1H,s); m/z 179(M+H)+.

Workup

  1. customto give a solid which
  2. extractionwas extracted into dichloromethane
  3. customThe organic phase was separated
  4. washwashed with water, saturated brine
  5. dry with materialdried (MgSO4)
  6. customEvaporation

Sources & evidence

ORD record
ord-2659a73d326241ff994f80f62863ac2d
Source dataset
uspto-grants-1997_11
Patent number
US05691349

Reaction notes

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